Fe(ClO4)3• 6H2O: A mild and efficient catalyst for one-pot three component synthesis of β-acetamido carbonyl compounds under solvent-free conditions

Molecular Diversity

Volumn 13, Issue 3, 2009, Pages 375-378

  Heravi, Majid M ^a   Behbahani, Farahnaz K ^a   Daraie, Mansoureh ^a   Oskooie, Hossein A ^a  

^a ALZAHRA UNIVERSITY   (Iran)

Author keywords

Acetamido Carbonyl Compounds; 3CC, MCR, Fe(ClO4)3; 6H 2O; One pot; Solvent free conditions; Three Component

Indexed keywords

ACETAMIDE DERIVATIVE; ACETOACETIC ACID; ACETONITRILE; ACETOPHENONE DERIVATIVE; ALDEHYDE; CHLORIDE; FERRIC ION; FERRIC PERCHLORRATE; UNCLASSIFIED DRUG; ACETONITRILE DERIVATIVE; ACETOPHENONE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; ESTER; IRON PERCHLORATE; KETONE; PERCHLORIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; ELECTRON; ONE POT SYNTHESIS; PRIORITY JOURNAL; CHEMISTRY; SYNTHESIS;

ACETAMIDES; ACETONITRILES; ACETOPHENONES; ALDEHYDES; BENZALDEHYDES; ESTERS; FERRIC COMPOUNDS; KETONES; PERCHLORIC ACID;

EID: 68349160370     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9118-z     Document Type: Article

References (29)

1. NK Terret M Gardner DW Gordon RJ Kobylecki J Steele 1995 Combinatorial synthesis-the design of compound libraries and their application to drug discovery Tetrahedron 51 8135 8173
2. RW Armstrong AP Combs PA Tempest SD Brown TA Keating 1996 Multiple-component condensation strategies for combinatorial library synthesis Acc Chem Res 29 123 131
3. LA Thomson JA Ellman 1996 Synthesis and applications of small molecule libraries Chem Rev 96 555 600
4. A Dömling I Ugi 2000 Multicomponent reactions with isocyanides Angew Chem Int Ed 39 3168 3210
5. J Barluenga AL Viado E Aguilar S Fustero B Olano 1993 1,3-Amino alcohols from 4-amino-1-aza dienes. Diastereo and enantioselective approach to the four diastereoisomers of the N-terminal amino acid component of nikkomycins B and BX J Org Chem 58 5972 5975
6. Enders D, Moser M, Geibel G, Laufer MC (2004) Diastereo and enantioselective synthesis of differently N,O-protected 1,3-amino alcohols with three neighbouring stereogenic centers. Synthesis 2040-2046
7. K Kobinata M Uramoto M Nishii H Kusakabe G Nakamura K Isono 1980 Neopolyoxins A, B, and C, new chitin synthetase inhibitors Agric Biol Chem 44 1709 1711
8. U Dähn H Hagenmaier H Höhne WA König G Wolf H Zähner 1976 Stoffwechselprodukte von mikroorganismen. 154. Mitteilung. Nikkomycin, ein neuer hemmstoff der chitinsynthese bei pilzen Arch Microbiol 107 143 160
9. M Mukhopadhyay B Bhatia J Iqbal 1997 Cobalt catalyzed multiple component condensation route to β-acetamido carbonyl compound libraries Tetrahedron Lett 38 1083 1086
10. Bhatia B, Reddy MM, Iqbal J (1994) Cobalt-catalysed three-component coupling involving ketones or ketoesters, aldehydes and acetonitrile: A novel one-pot synthesis of b-acetamido ketones. J Chem Soc Chem Commun 713-715
11. D Bahulayan SK Das J Iqbal 2003 Montmorillonite K10 clay: an efficient catalyst for the one-pot stereoselective synthesis of β-acetamido ketones J Org Chem 68 5735 5738
12. MM Khodaei AR Khosropour P Fattahpour 2005 A modified procedure for the Dakin-West reaction: an efficient and convenient method for a one-pot synthesis of β-acetamido ketones using silica sulfuric acid as catalyst Tetrahedron Lett 46 2105 2108
13. 3 generated in situ from the procatalyst BiOCl and acetyl chloride. Synlett 115-118 (Pubitemid 40094897)
14. 2O: an efficient Lewis acid catalyst for the one-pot multicomponent synthesis of β-acetamido ketones Tetrahedron 62 4059 4064
15. E Rafiee F Tork M Joshaghani 2006 Heteropoly acids as solid green Brønsted acids for a one-pot synthesis of β-acetamido ketones by Dakin-West reaction Bioorg Med Chem Lett 16 1221 1226
16. T Yakaiah G Reddy BPV Lingaiah B Narsaiah PS Rao 2005 Silica sulfuric acid: an efficient and recyclable catalyst for the synthesis of β-acetamido ketones in single pot Synth Commun 35 1307 1312
17. G Pandey RP Singh A Garg VK Singh 2005 Synthesis of Mannich type products via a three-component coupling reaction Tetrahedron Lett 46 2137 2140
18. E Rafiee F Shahbazi M Joshaghani F Tork 2005 The silica supported H3PW12O40 (a heteropoly acid) as an efficient and reusable catalyst for a one-pot synthesis of β-acetamido ketones by Dakin-West reaction J Mol Catal A: Chem 242 129 134
19. MM Heravi L Ranjbar F Derikvand FF Bamoharram 2007 H6P2W18O62: an efficient and reusable catalyst for one-pot synthesis of β-acetamido ketone and esters Catal Commun 8 289 291
20. AT Khan T Parvin LH Choudhury 2007 Iron(III) chloride-catalyzed convenient one-pot synthesis of β-acetamido carbonyl compounds Tetrahedron 63 5593 5601
21. MM Heravi FK Behbahani HA Oskooie RH Shoar 2005 Mild and efficient tetrahydropyranylation of alcohols and dehydropyranylation of THP ethers catalyzed by ferric perchlorate Tetrahedron Lett 46 2543 2545
22. MM Heravi FK Behbahani HA Oskooie RH Shoar 2006 Catalytic acetylation of alcohols and phenols with ferric perchlorate in acetic acid Catal Commun 7 136 139
23. MM Heravi FK Behbahani HA Oskooie RH Shoar 2005 Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid Tetrahedron Lett 46 2775 2777
24. MM Heravi V Zadsirjan FK Behbahani HA Oskooie 2006 Catalytic synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by ferric perchlorate J Mol Catal A: Chem 259 201 204
25. MM Heravi FK Behbahani RH Shoar HA Oskooie 2006 Ferric perchlorate: a novel and highly efficient catalyst for direct acetylation of THP ethers with acetic acid J Mol Catal A: Chem 244 8 10
26. HA Oskooie MM Heravi A Sadnia M Safarzadegan FK Behbahani 2007 Mild and efficient conversion of oximes into arylhydrazones catalysed by ferric perchlorate Mendeleev Commun 17 190 191
27. HA Oskooie MM Heravi A Sadnia F Jannati FK Behbahani 2007 Ferric perchlorate-catalyzed one-pot synthesis of alpha aminonitriles using trimethylsilylcyanide Synthetic Commun 37 2543 2548
28. 3 at room temperature Chinese Chem Lett 18 1357 1360
29. IN Rao EN Prabhakaran SK Das J Iqbal 2003 Cobalt-catalyzed one-pot three-component coupling route to b-acetamido carbonyl compounds: A general synthetic protocol for c-lactams J Org Chem 68 4079 4082